Top 10 FA Cup Upsets of All Time
When Underdogs Triumphed

Top 10 FA Cup Upsets of All Time: When Underdogs Triumphed
The Football Association Challenge Cup, popularly known as the FA Cup, is a competition rich in history and tradition. Since its inception in 1871, it has consistently delivered moments of sheer unpredictability, reminding us why football is called the "beautiful game." While it serves as a platform for elite clubs to showcase their dominance, it also provides an opportunity for lesser-known teams to make history. The underdog triumphs are what make the FA Cup unique, weaving tales of courage, grit, and the unrelenting human spirit. Here are the top ten FA Cup upsets of all time, where underdogs defied the odds and etched their names into football folklore.
1. Hereford United vs. Newcastle United (1972)
The magic of the FA Cup was on full display when non-league Hereford United defeated First Division Newcastle United in the third round replay. Newcastle entered the game as heavy favourites, but Hereford had other plans. Ronnie Radford’s iconic long-range strike levelled the match, sending the crowd into raptures. Ricky George’s extra-time goal sealed an unforgettable 2-1 victory for Hereford, marking one of the most celebrated moments in FA Cup history.
2. Sunderland vs. Leeds United (1973)
In a classic David versus Goliath encounter, Second Division Sunderland faced the mighty Leeds United in the 1973 final. Leeds were widely regarded as one of the best teams in Europe at the time, boasting a squad filled with stars. However, Ian Porterfield’s first-half goal and a heroic performance by Sunderland goalkeeper Jim Montgomery secured a 1-0 victory, making Sunderland the first second-tier team to win the FA Cup since 1931.
3. Wimbledon vs. Liverpool (1988)
Dubbed the "Crazy Gang," Wimbledon pulled off one of the biggest shocks in FA Cup history by defeating Liverpool in the 1988 final. Liverpool, then the dominant force in English football, were expected to cruise to victory. However, a first-half header from Wimbledon’s Lawrie Sanchez and Dave Beasant’s penalty save from John Aldridge ensured a 1-0 win. The triumph highlighted Wimbledon's tenacity and team spirit, leaving an indelible mark on the competition.
4. Wrexham vs. Arsenal (1992)
Few gave Fourth Division Wrexham a chance against reigning First Division champions Arsenal in the third round of the 1992 FA Cup. Arsenal took the lead through Alan Smith, but Wrexham staged an extraordinary comeback. Mickey Thomas equalised with a stunning free-kick, and Steve Watkin’s late goal sealed a 2-1 victory. This unforgettable upset remains one of the competition’s most celebrated moments.
5. Shrewsbury Town vs. Everton (2003)
In the third round of the 2002-03 FA Cup, Third Division Shrewsbury Town faced Premier League side Everton. Managed by former Everton striker Kevin Ratcliffe, Shrewsbury defied expectations with a heroic display. Two goals from Nigel Jemson, including a late winner, secured a 2-1 victory and sent shockwaves through English football.
6. Barnsley vs. Chelsea (2008)
Championship side Barnsley shocked Premier League giants Chelsea in the quarter-finals of the 2007-08 FA Cup. Kayode Odejayi’s header proved decisive as Barnsley secured a 1-0 win at Oakwell. The result demonstrated the magic of the FA Cup, where determination and belief can overcome the odds.
7. Lincoln City vs. Burnley (2017)
Lincoln City became the first non-league team in over a century to reach the FA Cup quarter-finals when they defeated Premier League side Burnley in the fifth round. Sean Raggett’s late header sealed a 1-0 victory, sparking scenes of jubilation among the travelling fans. Lincoln’s historic run highlighted the unpredictability and charm of the competition.
8. Bradford City vs. Chelsea (2015)
League One side Bradford City produced a sensational comeback to defeat Premier League leaders Chelsea in the fourth round of the 2014-15 FA Cup. Trailing 2-0 at Stamford Bridge, Bradford scored four unanswered goals to secure a remarkable 4-2 victory. The result epitomised the spirit of the FA Cup and remains one of its greatest shocks.
9. Oldham Athletic vs. Liverpool (2013)
Oldham Athletic, struggling in League One, faced Premier League giants Liverpool in the fourth round of the 2012-13 FA Cup. Matt Smith’s brace and a deflected goal by Reece Wabara helped Oldham secure a 3-2 victory. The result was a testament to the unpredictable nature of the competition, where lower-league teams can rise to the occasion.
10. Manchester City vs. Wigan Athletic (2013)
The 2013 FA Cup final saw relegation-threatened Wigan Athletic face a star-studded Manchester City side. Despite the odds, Wigan’s Ben Watson scored a dramatic injury-time header to secure a 1-0 victory. The triumph was a fairy-tale ending for Wigan, proving that belief and determination can achieve the extraordinary.
The Enduring Legacy of FA Cup Upsets
These unforgettable moments serve as a reminder that football is a game of possibilities. The FA Cup, with its rich history and tradition, continues to capture the imagination of fans worldwide. It provides a platform for underdogs to dream big and achieve greatness, inspiring generations of players and supporters alike.
What makes these upsets truly special is not just the triumph of the underdogs but the stories behind them; the resilience, the determination, and the unwavering belief that anything is possible. They remind us why we love the game, and why the FA Cup remains a cherished institution in the world of football.
About the Creator
Mutonga Kamau
Mutonga Kamau, founder of Mutonga Kamau & Associates, writes on relationships, sports, health, and society. Passionate about insights and engagement, he blends expertise with thoughtful storytelling to inspire meaningful conversations.




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